


It Feels Like The First Time

by ameliacareful



Category: Supernatural
Genre: Anal Sex, Dean's first time bottoming, I don't usually write smut, I will now go back to my happy gen existence, M/M, PWP, Realistic
Language: English
Status: Completed
Published: 2017-02-05
Updated: 2017-02-05
Packaged: 2018-09-22 03:55:03
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,558
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9582332
Author URL: https://archiveofourown.org/users/ameliacareful/pseuds/ameliacareful
Summary: Dean usually tops but Sam seems to enjoy bottoming so much that Dean kind of feels like a coward.  So Sam starts Dean on the process of getting used to anal.  Fingering.





	

            “Are you sure?” Sam asks.

            Dean is sure. He’s not a coward. Sam loves it, there’s got to be something great about it. He did the thing with the enema bulb and got really clean which was, lets face it, gayer than gay, but Sam has done it for him so time to man up. And he now feels both simultaneously weirdly cleaner and dirtier than he ever has before because after he used the little bulb thingy and squirted water up his ass a couple of times and stuck a soapy finger up there, he still feels conscious of his ass in a way he normally doesn’t…

            “I’m not sure I’m clean—” Dean blurts out.

            Sam grins. “Dean.”

            “I mean, I think I’m pretty clean…”

            “Shut up,” Sam says.

            Dean is lying on his bed, on his memory foam, drying his balls after the whole bath and stuff. Sam is leaning in the doorway, wearing only jeans, barefoot, looking like something off a gay men’s Hunter’s calendar and why the fuck is Dean even thinking that? He never thinks like that they’re just who they are and what they do doesn’t even need a label. Maybe Sam needs a label with his weird obsession about what he puts in his body and his exercise.

            “I’ll be back.” Sam pads off and Dean lays there and tries not to think about what he’s agreed to. He’s not sure what he’s agreed to. Sam says he’s not going to fuck Dean right away. ‘You work up to that,’ he says. ‘Your ass is not a vagina,’ he says. ‘We’ll just play and when you say stop, we’ll stop.’

            It was Dean’s idea.

            He is insane. Why did he even suggest this?

            Because Sam seems to love what he does to Sam’s ass. Sam can take him. And he can’t stand that Sam can take him and he can’t. Take. Sam.

            So.

            Sam pads back in with beer.

            He hands Dean a bottle and puts the rest down. Slides in the bed next to him and opens one himself. He takes a drink. Then he runs a cold finger over Dean’s nipples and Dean startles. “Fuck!”

            “Jumpy?”

            “Your fingers are cold.”

            Sam laughs.

            “You’re an asshole.”

            “No, it’s your asshole we’re talking about.”

            Dean snorts.

            Sam reaches over and runs his fingers over Deans balls. Dean loves that and reaches for Sam but his brother shakes his head. “Just relax. Drink your beer and just feel what I’m doing.”

            Dean gives him a look.

            “You’re a control freak,” Sam says.

            “Look who’s talking,” Dean says.

            Sam laughs quietly. “I am not getting into that.”

            “At least take your pants off.”

            Sam graciously does. Dean is not insecure about his looks but Sam’s long legs, well, it took awhile for Dean to get over the genetic lottery. Sam is tall and straight and Dean is tall but not as tall and bow-legged. Eventually he figured out that people find that attractive. Sam in particular. But it’s hard to think ‘bow-legged’ and not think, you know, bad cowboy cartoons. Sam’s legs, on the other hand, sometimes make him believe Chuck may not be a total asshole. But then Sam is self-conscious about everything. His beautiful hands. He thinks his forehead is too big, his chin is too short. He worries about getting fat. Dean knows that Sam pretty much worships Dean’s looks. He’s felt Sam’s finger’s trace his lips, his nose, his jaw. Felt Sam’s adoration of his shoulders, his freckles, his biceps, his pecs, his calves, his feet, his dick, his asshole…

            Which brings them to right now and his sudden realization that Sam has been gently playing with his balls and the sudden rush of heat and arousal.

            Sam stops. Takes his beer and puts it on the bedside table.

            Dean is not happy he stops but Sam is putting lube on his index finger.

            “It’s going to be cold,” he says.

            Dean nods.

            Sam waits a moment, then reaches down and runs his finger around Dean’s asshole.

            It’s not the first time Sam has played around his asshole. Dean doesn’t mind being rimmed but honestly it doesn’t excite him as much as it does Sam. Sam loves being rimmed. Dean likes how much Sam loves rimming him but there isn’t much in the way pleasurable nerve endings there. Still, the cold is interesting and having Sam watch him him that way…Sam is aroused. That is arousing.

            Then Sam pushes a little against Dean’s asshole with his finger tip.

            “Okay?” Sam asks.

            Dean nods, pulling his knees up. He keeps his eyes on Sam.

            Sam shifts around the bed so he’s between Dean’s knees. “So gorgeous. Oh my God, Dean. You’re so fucking gorgeous.”

            He wants to say, “It’s an asshole,” but he loves Sam’s so he knows better. Loves the heat and the tightness of Sam. Loves when Sam lowers himself onto him and he can start thrusting and Sam throws his head back and whispers, ‘So full with you.’ Loves the way Sam squeezes.

            “I’m going to push in a little, tell me if you want me to stop,” Sam says.

            “Okay,” Dean says.

            It’s weird. It burns a little. He tries to relax.

            “There’s two rings of sphincter,” Sam says. “That’s the part you have to get past.”

            “Are you in?” Dean asks.

            Sam chuckles. “Not even the first knuckle. Just the first ring of muscle. Just relax. I’m not moving. Get used to it.”

            God, he feels like a fucking virgin. He feels like Sam’s finger is the size of Sam’s dick. He breathes and lets himself relax. Lets himself fell it. “Okay,” he says. “Keep going.” He feels Sam push a little and he pushes against Sam’s finger. Sam lets him decide him much, holding still and letting him push until the finger goes past the second ring.

            “I’m in,” Sam says.

            “Stop,” Dean says, feeling the burn, feeling the discomfort. Sex hasn’t been uncomfortable in a very very long time. He breathes, feeling the fullness, his body trying to push it out, trying to accommodate.

            “Squeeze,” Sam says.

            Dean does, bearing down.

            Sam laughs with delight. “I can feel it,” he says.

            Dean looks between his knees and Sam’s face makes his dick harden. It had softened—nothing about this had felt sexy but now it was a little. Sam was happy. Sam liked this. Sam didn’t need anything more than Dean letting him do this, Dean feeling Sam’s finger in him and Sam’s finger wasn’t feeling as strange as it had. Hot. He felt almost as if he could feel the ridges of Sam’s fingerprints but that was crazy.

            “More lube?” Sam asks.

            “Yeah,” Dean says.

            Sam pulls his finger out slowly.

            They go through it all again. It’s all encompassing, the world narrowed down to this; to them, to this finger and Sam’s pleasure and the feeling Dean has and Dean moving. Sam holds still and Dean moves down on him slowly until Sam’s finger is in him and this time, slowly, steadily, he can take it in. All the world in Sam’s long finger.

            “Second knuckle,” Sam says.

            “Keep going,” Dean says. It isn’t particularly pleasurable. But it’s okay and he thinks it was a first step and eventually he’ll be able to take Sam’s dick. Not today, but eventually. Make Sam happy.

            Then Sam starts moving his finger and the feeling…the feeling. Dean can’t actually explain it. It’s like pleasure but he can’t figure out where it is.

            “What…”

            “That’s your prostate,” Sam says.

            It’s elusive. It’s not like stroking his dick. He can’t describe it. Oh God he wants to find it. He has his eyes closed and his teeth clenched. He chases it but he can’t find it. It’s a warmth, a glow. It’s diffuse. It’s not like anything he’s felt before. He wants it.

            “You want me to stop?” Sam asks.

            “No,” Dean says.

            Then Sam’s mouth is on his dick and he almost doesn’t want it because it’s so strong and the feeling from his finger is so much harder to locate and Dean wants the strong feeling but it swamps that internal feeling so he can’t find it. He wants to say stop but he wants to come and the feeling of wanting is coming from his dick but also this other place and it comes from his dick and he comes and it’s really strong and he comes so hard his toes curl but then inside he can feel Sam.

            “Stop!” he says.

            Sam is laughing and gently, oh so gently, starts pulling his finger out.

            Dean is still having aftershocks and it’s too much. “Don’t!” he says.

            “I can feel you,” Sam whispers. “I can feel you clenching around me.”

            “Fuck you,” Dean says, “fuck you don’t, don’t…”

            “I did,” Sam says, “I finger fucked you Dean.”

            Dean starts laughing, helplessly. He wants it out, he never wants it to end. It is awesome.

            Finally Sam pulls his finger out and the throbbing slowly ebbs through his body.

            Dean opens his eyes and he’s in his room.

            “Yeah?” Sam asks.

            “Fuck you,” Dean says.

            “Maybe not tonight,” Sam says. He folds against Dean and Dean wraps his arms around his brother.

            As Dean is drowsing he hears Sam whisper, “Thank you.”

**Author's Note:**

> Most fanfic treats anal sex as if anal sex and vaginal sex were very similar. They're not. I don't write smut but I wanted someone to write a fanfic that treated anal sex as different yet make it hot. I finally decided that even though I don't usually ship and I write gen, if I wanted this to happen I should just shut up and write it. I don't know if this is hot or if it really works but here it is.
> 
> If you are interested in the specifics of finding the male prostrate, this is a very useful site and video.
> 
> http://mrracy.com/how-to-find-your-prostate/
> 
> After the video, you will never look at a sports drink bottle the same way again.
> 
> May you never (as I sometimes do) read a sex scene and think 'but poop!'


End file.
